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65 Highland Ave, Middletown
$399,000
3 Beds ⋅ 2 Baths ⋅ 24209628 MLS
Welcome to this beautifully remodeled Brick Cape set on a level .41-acre lot with brick-wall-lined driveways, this 1,543-square-foot home offers 3 bedrooms and 2 full baths, including a first-floor primary bedroom-perfect for those looking for one-level living now or in the future. Both baths have been remodeled, the interior has been freshly painted, and there are sparkling hardwood floors throughout much of the home. The brand-new kitchen features beautiful quartz countertops, new cabinetry, stainless steel appliances, and a spacious dining area that's perfect for everyday meals or gathering with family and friends. The living room offers a cozy fireplace, while the finished basement family room provides even more space to relax, entertain, or create a room that fits your lifestyle. Outside, the 3-car garage, with brand-new overhead doors and openers offers plenty of room for vehicles, storage, hobbies, or whatever you may need. Additional updates include mostly all new windows, brand-new central air, newer roof, with brand-new gutters and leaders, many of the important updates have already been taken care of. Whether you're buying your first home, looking for more room to grow, or dreaming of a home that can comfortably carry you into your next chapter, 65 Highland Ave is a special place with so much to appreciate.

65 Highland Ave, Middletown

63 Millbrook Rd, Middletown
$385,000
3 Beds ⋅ 2 Baths ⋅ 24210439 MLS
Welcome to this inviting contemporary-style single-family home offering 3 bedrooms, 2 full bathrooms, and approximately 1,963 square feet of living space. Situated on a level .45-acre lot, this well-maintained 1975 home offers comfortable living spaces, desirable updates, and exceptional versatility. The spacious living room features a striking cathedral ceiling, creating an open and airy atmosphere. The kitchen has been updated with new appliances, while newer carpeting adds a fresh, updated feel throughout the home. A standout feature is the finished basement, complete with its own kitchen, offering excellent additional living space and flexibility. This area is ideal for an in-law suite, extended family, guests, home office, or recreation space, providing numerous possibilities to suit your needs. Enjoy outdoor living from both the front and rear decks, perfect for relaxing, entertaining, or enjoying the generous level property. Additional features include a two-car attached garage and central air conditioning. With its spacious layout, flexible finished lower level, updated kitchen appliances, outdoor living spaces, and convenient attached garage, this contemporary home offers a wonderful combination of comfort and versatility. **This is a short sale. **

63 Millbrook Rd, Middletown

Bow Ln, Middletown
$67,000
24210034 MLS
This unique parcel of land sits some 500 feet above the City of Middletown. While it has served me well as a peaceful recreational spot for the last 13 years, it is now time to let it go to someone else who might enjoy it. It's surrounded by other similar vacant and wooded plots of land due to there being no paved road or other services for some 800 feet in from the top of Bow Lane. Think 4-wheeling and dirt bike fun on the weekends while the rest of the family picnics under the shade awaiting your return. Potential buyers will need to do their own due diligence before they consider this purchase. No claims of suitability for any particular purpose are being represented, here. There is an easement in the deed requiring the owner to provide access to Bow Lane to the 5.5 acre parcel that sits directly behind this one. NOTE: At this time that parcel is also currently listed for sale.

Bow Ln, Middletown

227 E Main St, Middletown
$600,000
9 Beds ⋅ 6 Baths ⋅ 24209312 MLS
Exceptional Mixed Use 3-Unit Investment Opportunity in Middletown! Well-maintained three-unit property offering the feel of townhouse-style living with the income potential of a multifamily investment. Each spacious unit features 3 bedrooms, 1 full bath, 1 half bath, an eat-in kitchen, abundant natural light, basement storage, and washer/dryer hookups. A standout feature is the private under-building garage for each unit with direct access, plus ample off-street parking and a rear driveway. Separate utilities provide added convenience for ownership and management. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. An excellent opportunity for an investor or owner-occupant looking to generate rental income while building equity. Property being Sold As Is. Agent/Owner related.

227 E Main St, Middletown

225 Pearl St, Middletown
$579,900
6 Beds ⋅ 3 Baths ⋅ 24208519 MLS
Group showing Sunday, 10/18, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desirable street close to Downtown Middletown, the property offers easy access to restaurants, shopping, Wesleyan University, major routes, and everything the downtown area has to offer. Whether you're looking to add a solid three-family to your investment portfolio or live in one unit while collecting rent from the other two, this is the type of multifamily property that is getting harder to find. Great location, private outdoor spaces, garage, strong updates, and three income-producing units all in one property. Don't wait on this one-schedule a showing and see the opportunity for yourself!

225 Pearl St, Middletown

15 Rising Trail Dr Unit 15, Middletown
$239,900
3 Beds ⋅ 2 Baths ⋅ 24209015 MLS ⋅ Beacon Hill Towne Homes BLDG.
Experience the timeless elegance in this beautiful 3-bedroom, 1.5-bath townhome offering 1,232 sq. ft. of bright, comfortable living space. This refined residence features three spacious bedrooms plus a versatile Flex room with skylight on the 3rd floor, seamlessly blending classic architectural details with modern, open-concept living.. This unit also includes a 1-car under unit garage, adding convenience with additional storage and a new roof. Enjoy private outdoor living on your own personal deck and take advantage of the community pool just around the corner on warm summer days. Conveniently located close to a variety of popular restaurants, shopping and biking trails all within a prime Middletown location. Perfectly positioned close to Route 9 and I-91, this home offers the ultimate lifestyle of comfort, convenience, and commuter ease, all within a well-maintained association with a low HOA of only $450 per month. Ready to schedule your showing today.

15 Rising Trail Dr Unit 15, Middletown

42 Grand St, Middletown
$369,900
6 Beds ⋅ 2 Baths ⋅ 24208513 MLS
Ideal for an investor or owner occupant this 2 family home offers 2 units 5 rooms with 3 bedrooms each. The first floor unit with hardwood floors 3 spacious bedrooms, refreshed bath, and a kitchen with a walk in pantry. The second floor has been remodeled with 3 bedrooms and the primary bedroom with a large walk in closet or storage room. Updated kitchen, laminate floor, white cabinets and walk in pantry and refreshed full bath with tile tub surround and floor. This property has a front porch and a rear porches. A walk up attic offers additional space with an option for future expansion. A full basement with a full bath and a finished room. Furnaces and Hot water heaters replaced in 2021. Driveway which will allow for 2 cars of off street parking. Great opportunity to add to a portfolio.

42 Grand St, Middletown

Bow Lane, Middletown
$95,000
24208129 MLS
5.5 ACRES | MIDDLETOWN, CT DEVELOPMENT & INVESTMENT OPPORTUNITY Bring your vision to this approximately 5.5-acre parcel of raw, unimproved land in Middletown. An opportunity for builders, developers, investors, or buyers interested in exploring the property's future potential. Property is being sold in its current unimproved condition. Public assessor records indicate the parcel as landlocked. Buyer and buyer's representatives are responsible for conducting their own due diligence regarding legal access and/or easements, road frontage , subdivision and buildability, zoning and permitted uses, wetlands, septic and well requirements, utilities, surveys, engineering, road improvements, and any municipal or governmental approvals required for their intended use. Approximately 5.5 acres offering an opportunity for the right buyer to investigate the possibilities and potential of this Middletown property.

Bow Lane, Middletown

35 Sonoma Ln Unit 35, Middletown
$589,000
2 Beds ⋅ 3 Baths ⋅ 24208777 MLS ⋅ Sonoma Woods BLDG.
Homes in Sonoma Woods don't come available often, and Unit 35 offers one of the largest models in this sought-after 55+ Middletown community. With 2 bedrooms, 2.5 baths, walkout basement with an exercise or craft room, and nearly 2,000 sq ft of living space, this home delivers the ease of condo living without giving up the space you want. The comfortable main level features a fireplace and a heated sunroom overlooking the back of the property, creating additional year-round living space and leading directly onto the deck for relaxing or entertaining. The full walkout basement offers more than 1,000 sq ft, with a portion already finished for even more usable space while still providing plenty of room for storage, hobbies, a workshop or future possibilities. An attached garage, natural gas heat and central air add everyday convenience. Built in 2005, this spacious unit offers a great opportunity for buyers looking to right-size without feeling like they have to squeeze into their next home. With limited turnover in Sonoma Woods, opportunities like this can be hard to find. If you've been waiting for a home in this community, could Unit 35 be the one worth making a move for?

35 Sonoma Ln Unit 35, Middletown

25 Wanda Ln, Middletown
$579,900
4 Beds ⋅ 3 Baths ⋅ 24208360 MLS
NEW PRICE - $579,900! Beautiful 4-Bedroom Colonial | Solar Energy Savings | Private Pool | Newly Expanded Driveway! Welcome to 25 Wanda Lane, Middletown! This beautiful and spacious 4-bedroom, 2.5-bath Colonial offers approximately 2,226 sq. ft. of above-ground living space, situated on approximately 0.35 acres. Built in 2000, this home combines comfortable family living, energy savings, and great outdoor entertaining spaces. MAJOR ENERGY-SAVING ADVANTAGE - LARGE SOLAR SYSTEM! Enjoy the benefits of an existing large solar energy system that generates substantial electricity throughout the year. Monthly Eversource statements document solar generation and electricity credits, helping offset household electricity costs and providing the potential for significant annual savings. NEWLY COMPLETED DRIVEWAY EXPANSION! A major recent exterior improvement features an expanded driveway with attractive decorative pavers and newly installed retaining wall blocks. This improvement provides additional paved parking space, enhances curb appeal, and creates a more attractive approach to the home and attached two-car garage. Inside, the home features a welcoming two-story foyer, hardwood floors, a kitchen with granite countertops and pantry, a cozy fireplace, and generous living and dining areas. The spacious primary bedroom suite includes a walk-in closet. Additional conveniences include central air conditioning, main-level laundry, and an attached two-car garage. The par

25 Wanda Ln, Middletown

142 Crystal Lake Rd, Middletown
$369,900
2 Beds ⋅ 1 Baths ⋅ 24207901 MLS
LAKESIDE LIVING ON CRYSTAL LAKE! Welcome to 142 Crystal Lake Road, where everyday living feels like a getaway. Set on picturesque Crystal Lake, this charming 2-bedroom, 1-bath home offers the rare opportunity to enjoy waterside living from your own backyard. Step inside and you'll find 1,188 square feet of comfortable living space with a warm, inviting feel. The home features an updated kitchen, updated bathroom, and an updated primary bedroom, along with important mechanical updates including the boiler and water heater. A stone fireplace/pellet stove creates a cozy focal point for relaxing on cooler evenings. Outside, the private deck is the perfect place to enjoy morning coffee, dinner overlooking the water, or quiet evenings taking in the changing seasons. With direct lake frontage, you'll have the opportunity to enjoy kayaking, fishing, and the peaceful beauty of Crystal Lake right at home. A detached one-car garage provides additional convenience and storage, while the approximately half-acre lot offers a wonderful balance of privacy and waterfront enjoyment.

142 Crystal Lake Rd, Middletown

74 Boston Rd, Middletown
$379,000
4 Beds ⋅ 2 Baths ⋅ 24207911 MLS
Welcome to 74 Boston Rd in Middletown, CT, a beautifully renovated home that has been gutted down to the studs and rebuilt with nearly everything brand new. This spacious property offers 4 bedrooms plus a bonus room previously used as a children's bedroom, along with 2 full bathrooms. Designed to feel like new construction, the home features a new roof with new plywood and shingles, new siding with insulation, new interior framing, drywall, flooring, doors, brand-new energy-efficient LED light fixtures, recessed lighting in the living room, dining room, and large laundry room, plus double-pane windows throughout. The updated kitchen includes new cabinets, quartz countertops, refrigerator, dishwasher, microwave, stove/oven range, and faucet. Both bathrooms include new vanities, faucets, toilets, porcelain tile flooring, and porcelain tile shower walls. Brand New Driveway. Major upgrades also include new insulation inside the walls, all-new plumbing pipes, a brand-new gas line, a new tankless high-efficiency gas boiler for heat and hot water, a brand-new 200 AMP electrical panel, and all new electrical wiring, outlets, and switches. Permits were pulled for electrical, HVAC, plumbing, and general construction, and all permits were successfully closed with inspections passed. Sitting on a huge 0.97-acre lot with a brook behind the yard, this move-in-ready home offers modern comfort, space, and peace of mind, like a new construction would.

74 Boston Rd, Middletown

609 Newfield St, Middletown
$599,609
2 Baths ⋅ 24207348 MLS
Located along the highly visible Newfield Street corridor, 609 Newfield Street is a converted mid-century ranch now used as professional office space. Originally built in 1950 as a single family home, the 1,500 sq ft building has been fully adapted for commercial use and currently houses Innovative Properties. The layout provides multiple private offices, meeting areas, and a welcoming reception space. The 1.09-acre lot offers ample off-street parking and room for exterior improvements. Its flexible design also makes the property a strong candidate for group home use. The owner is willing to complete modifications or provide a credit for required updates. Owner financing is available. Located within Middletown's NPC zone, the property supports a wide variety of professional, service, and light retail uses, including medical, dental, legal, salon, specialty retail, or care-based operations. With strong drive-by exposure on Route 3, convenient neighborhood access, and close proximity to local schools and amenities, 609 Newfield Street offers excellent visibility and adaptability for a business or organization seeking a ready-to-occupy space in one of Middletown's most active commercial corridors. AGENT OWNER

609 Newfield St, Middletown

27 Fairview Ave, Middletown
$244,900
4 Beds ⋅ 1 Baths ⋅ 24205927 MLS
Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. Seller believes there to be oak hardwood under the carpets. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

27 Fairview Ave, Middletown

61 E Main St, Middletown
$1,395,000
21 Beds ⋅ 9 Baths ⋅ 24206879 MLS
Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

61 E Main St, Middletown

201 College St Unit 10, Middletown
$199,000
2 Beds ⋅ 2 Baths ⋅ 24205649 MLS ⋅ Hamlin Court BLDG.
Welcome to a bright and updated townhouse-style condo offering a comfortable layout and several features that set it apart. The first floor has been refreshed with luxury vinyl plank flooring and includes a spacious living area, dining space, and modern-style kitchen. Upstairs, two bedrooms are accompanied by a versatile bonus room featuring a vaulted ceiling and skylight, offering an ideal spot for a home office, reading room, gym, or creative space. Newer windows installed in 2020. One of the best highlights is the private composite deck overlooking the courtyard, creating an enjoyable outdoor space without the maintenance of a traditional yard. The unit also includes in-unit laundry, dedicated enclosed basement storage, 1 parking spot in the private lot and some overflow parking. With the association currently having capacity for rentals, this condo offers flexibility for an owner occupant or investor. Conveniently located next to Wesleyan's art building, near Downtown Middletown, Wesleyan University, shopping, dining, and major commuter routes. Cash buyers only.

201 College St Unit 10, Middletown

1231 Washington St Unit 2, Middletown
$224,500
3 Beds ⋅ 1 Baths ⋅ 24205455 MLS ⋅ Woodgate BLDG.
Enjoy one of a select few of the largest townhouse end units in the complex offering 1,109 square feet of vast living space. Nestled in a popular, well-maintained community, this home combines convenience, comfort and peace of mind with nothing to do but unpack and enjoy. Recent complex-wide improvements include new roads with abundant guest parking, new siding, roofs, and decks giving the community a fresh, updated appearance. Additional highlights include a private entrance, in-unit washer and dryer, 6 panel doors, and hot water heater only four months old. Step inside to discover an inviting open floor plan featuring a spacious living room with soaring vaulted ceilings that fill the space with natural light and create an airy, welcoming atmosphere. The main level offers a remodeled kitchen with newer cabinetry, appliances and tile flooring. Enjoy an updated full bath with deep tub / shower combination, newer glass doors, plus two generously sized bedrooms, each with sliding glass doors leading to an oversized deck-perfect for morning coffee, outdoor dining, or simply relaxing. Upstairs, a third bedroom provides flexible space ideal for guests, a home office, workout room, or additional living area. Conveniently located near shopping, restaurants, major commuter routes, and just 2.2 miles to Wesleyan University, this home presents an excellent opportunity for owner-occupants and investors alike. Cash, Conventional and CHFA Conv Financing only. Special Assessment ends 10/38.

1231 Washington St Unit 2, Middletown

Unit 2-41 Webster Ln Unit 145, Middletown
$689,000
2 Beds ⋅ 2 Baths ⋅ 24205132 MLS
Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an ideal blend of comfort, style, and convenience. Inside, you'll find elegant white cabinetry, quartz countertops, and a spacious walk-in pantry that combine beauty with functionality. Hardwood flooring flows throughout the main living areas, while the bathrooms and laundry room feature durable tile flooring. A bright bay window in the front room fills the space with natural light and offers sweeping views. Outside, the private rear patio provides the perfect setting for relaxing or entertaining. Additional highlights include natural gas heating and central air conditioning for year-round comfort. Some photos are of similar homes and may include optional upgrades. Agent/owner related.

Unit 2-41 Webster Ln Unit 145, Middletown

500 Washington St Unit #9, Middletown
$119,000
1 Beds ⋅ 1 Baths ⋅ 24204389 MLS
*** BRAND NEW MOBILE HOME - Modern, Stylish & Ready for You! *** Be the first to call 500 Washington Street #9 home! Located in Middletown Mobile Home Park, this brand-new 1-bedroom, 1-full-bath mobile home offers fresh, modern living with everything new from the start. A welcoming 6' front porch adds charm and the perfect spot to relax outdoors. Inside, enjoy a bright, thoughtfully designed interior featuring a beautiful kitchen with new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. With 200-amp electrical service and an efficient, easy-to-maintain layout, this home offers comfort, convenience, and the peace of mind that comes with owning brand new. The new mobile home is now onsite with anticipated move-in availability November 13th. Why renovate when you can start fresh? Don't miss this opportunity to be the very first owner - schedule your showing and make #9 yours! ***Note: Sketch is a rendering of the New Mobile Home Model. Colors and Details may differ. New Mobile Home on Pad Site - Taxes to be determined. Purchaser to verify with local municipality. MMHP LLC - one of the parties to the LLC has an active real estate license***

500 Washington St Unit #9, Middletown

122 Newfield St Unit 3A, Middletown
$329,900
3 Beds ⋅ 2 Baths ⋅ 24201404 MLS ⋅ Arawana Estates BLDG.
Welcome to Arawana Estates, where historic charm meets modern comfort in a truly unique setting! Located within a beautifully converted mansion, this rarely available penthouse-style condo offers a spacious & distinctive layout filled with character & natural light. High ceilings, hardwood floors, recessed lighting, oversized windows & custom built-ins create a warm & inviting atmosphere throughout. The updated kitchen features crisp white cabinetry, leathered granite countertops with breakfast-bar seating, stainless steel appliances & a new Bosch dishwasher. Beautifully appointed baths offer granite finishes, subway tile & a relaxing soaking tub. The impressive primary bedroom is a standout, offering generous proportions, beautiful hardwood flooring, a fireplace & extensive custom built-in cabinetry & shelving. In-unit laundry & abundant storage add everyday convenience. Set within an intimate 6-unit community, Arawana Estates is surrounded by expansive lawns, mature trees, distinctive stonework & picturesque views, creating a peaceful & private setting just minutes from everything Middletown has to offer. Conveniently located near Wesleyan University, downtown Middletown, restaurants, shopping, parks, trails & public transportation. Veterans Memorial Park is also nearby, offering a community pool, splash pad & walking trails. A rare opportunity to own a one-of-a-kind residence combining historic architecture, modern updates, generous living space & beautiful surroundings.

122 Newfield St Unit 3A, Middletown

17 E Lake Pl, Middletown
$329,000
3 Beds ⋅ 2 Baths ⋅ 24204544 MLS
***Seller is ready for the next chapter and welcomes reasonable offers*** Welcome home to this beautifully updated property tucked away on a quiet cul-de-sac offering privacy, ample parking, and a spacious backyard perfect for relaxing, entertaining, or enjoying the outdoors. Inside, you'll find an updated and upgraded kitchen and bathrooms, complemented by newer vinyl windows and a newer roof for added peace of mind. A large two-car garage provides plenty of room for vehicles along with valuable additional storage. Conveniently located near the Cromwell/Middletown line, this home is a commuter's delight with easy access to Route 9, Route 372, and I-91. Enjoy being just minutes from restaurants, shopping, supermarkets, Wesleyan University, Wadsworth Falls State Park, Powder Ridge Park and Resort and many other area amenities. Offering a great combination of privacy, convenience, updates, and accessibility, this home is ready for its next chapter. AS-IS sale. Inspection for buyers' information only. Some photos virtually staged for illustration purposes only.

17 E Lake Pl, Middletown

85 Freeman Rd, Middletown
$749,900
4 Beds ⋅ 3 Baths ⋅ 24204169 MLS
NEW CONSTRUCTION MODERN COLONIAL Beautiful 4-bedroom, 21/2-bath Modern Colonial privately situated on 1.8 acres of rolling country hills. Currently under construction to be complete mid Nov. Exterior features include vinyl siding, Harvey windows, architectural shingles, Trex front porch with white railings, & paved driveway not yet complete. The lot will be professionally graded, topsoiled, and seeded. The approximately 2,232 sq. ft. home features 31/4" natural-finish white oak flooring, tile baths, square-edge flat trim, recessed lighting, & inset floor registers. The kitchen offers white shaker cabinets, quartz counters, navy-blue eat-at island, stainless farmhouse sink, built-in hood, propane stove, & an appliance allowance. The family room features a gas fireplace. The primary suite includes a coffered ceiling with crown molding, walk-in closet with custom shelving,& bath with double vanity, quartz counter, and walk-in rain-head shower. Four bedrooms include a flexible 4th bedroom/bonus room, plus second-floor laundry. Additional features include white bathroom vanities, quartz bath counters, hydro-air heating/cooling, Insta-hot combination boiler/hot water system, 200-amp service, well & septic, oversized 2-car garage with openers, unfinished basement, and Trex rear deck. Adjacent 2.8-acre lot also available, with plans for a home in the same Modern Colonial style. AI-enhanced photos of anticipated finished home/landscaping- actual appearances may vary

85 Freeman Rd, Middletown

54 Washington St, Middletown
$889,000
1 Baths ⋅ 24203918 MLS
PERMIT IN HAND - READY TO BUILD! Located in the heart of Middletown and within walking distance of an abundance of downtown amenities, 54 Washington Street presents an exceptional redevelopment opportunity in a highly desirable location. Formerly home to the Italian American Club, this distinctive property offers both character and history while being fully positioned for its next chapter. The property has received zoning approval for conversion from a community/event space into 19 residential units, with additional space incorporated for a superintendent. A tremendous amount of the development work has already been completed. The property includes professionally engineered 19-unit build-out plans, along with stamped electrical and plumbing plans. With major building systems professionally designed, code-compliant, and permit-ready, a new owner can move directly toward the construction phase-eliminating much of the time, cost, and uncertainty typically associated with the planning and approval process. Adding even greater value, the Town has approved 19 parking spaces directly across the street, adjacent to the police station. For the savvy investor or developer seeking a residential conversion opportunity with approvals, plans, parking, and a prime downtown location already in place, 54 Washington Street offers a rare opportunity to step into a project that is truly ready to build.

54 Washington St, Middletown

105 Spring St, Middletown
$305,900
5 Beds ⋅ 2 Baths ⋅ 24203700 MLS
**Multiple Offers, Highest and Best Due EOD Wednesday, 9/9/26** Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating systems, keep operating simple. Additional highlights include enclosed porches, new flooring and updates throughout, an open unfinished basement with plenty of storage, and off-street parking for multiple vehicles. Appliances will be provided with the right offer. Close to Wesleyan University, hospitals, parks, and commuter routes to Hartford and the shoreline. Easy to show - schedule today! Agent Owner

105 Spring St, Middletown

147 Old Mill Rd, Middletown
$435,000
3 Beds ⋅ 2 Baths ⋅ 24203125 MLS
This charming three-bedroom, one-and-a-half-bath English Tudor sits on a landscaped corner lot and offers a wonderful mix of classic details and modern updates. The beautifully updated kitchen features white and gray cabinetry, quartz countertops, a farmhouse sink, breakfast bar, stainless steel appliances, and plenty of storage and workspace. From there, the layout flows into the dining room with its original corner hutch, followed by a tiled sunroom that leads out to the patio. The living room features hardwood flooring, built-in bookcases, and a wood-burning fireplace. A convenient half bathroom completes the main level. Upstairs, you'll find a primary bedroom with a walk-in closet, two additional bedrooms, and a tastefully renovated full bathroom. Approximately 430 square feet of finished space in the lower level includes a family room with a bar, workshop, laundry room with a utility sink, and additional storage. The property also includes a detached two-car garage and paved driveway.

147 Old Mill Rd, Middletown

74 Grove St, Middletown
$365,000
4 Beds ⋅ 2 Baths ⋅ 24202551 MLS
Welcome to this beautifully remodeled two-family home ideally located within walking distance of vibrant downtown Middletown! This property offers the perfect blend of modern updates, spacious living, and unbeatable convenience. Both units have been fully remodeled with new appliances and updates throughout, making this an excellent opportunity for an owner-occupant, investor, or multi-generational living arrangement. Enjoy the added charm and versatility of enclosed back porches, perfect for relaxing, extra storage. A standout feature is the walk-up attic, offering approximately 650 additional square feet of living space-an incredible opportunity to create additional bedrooms, an office, recreation room, or whatever best suits your needs. Natural gas heat and hot water, separate utilities. Common laundry area in the basement with brand new washer and dryer. Step outside and enjoy everything Middletown has to offer, with parks, restaurants, shops, and downtown attractions all just a short walk away. Located in the heart of a lively and growing community, this home combines convenience, character, and future potential. Move-in ready, fully updated, and in a fantastic location-this is a two-family opportunity you won't want to miss!

74 Grove St, Middletown

774 Long Hill Rd Unit 774, Middletown
$299,900
3 Beds ⋅ 2 Baths ⋅ 24201757 MLS ⋅ Ridgely Condo Ii BLDG.
Welcome to 774 Long Hill Road, a meticulously maintained 3-bedroom, 1.5-bath townhouse in the desirable Wesleyan Hills community. Lovingly cared for by the same owner for the past 20 years, this home offers durable, easy-care laminate flooring throughout and annually serviced mechanicals for added peace of mind. The spacious eat-in kitchen opens through sliding doors to a large private deck, perfect for outdoor dining and relaxation. A finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a new washer, thermal windows, low-maintenance vinyl siding, two parking spaces and a roof approximately 10 years old. Set across 288 scenic acres, Wesleyan Hills offers a truly special neighborhood setting with ponds, fields, wooded open spaces and approximately two miles of walking paths connected by charming footbridges and tunnels. The community is also home to the historic Barns at Wesleyan Hills, a picturesque event venue overlooking the water. Just moments away, the beautiful Wadsworth Mansion and surrounding parklands offer miles of additional trails, seasonal events and popular outdoor summer concerts. Enjoy peaceful surroundings and a wonderful sense of community, all just three miles from vibrant downtown Middletown.

774 Long Hill Rd Unit 774, Middletown

145 Monarca Dr, Middletown
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 24202531 MLS
A one-of-a-kind custom-built new construction home that must be experienced in person to be appreciated. This modern contemporary farmhouse-style ranch sits on 2.38 acres of private land, positioned at the end of a cul-de-sac on a private road. From the moment you arrive, the exterior makes a lasting impression. Stone walls frame the driveway, guiding you past a thoughtfully designed approach w/a waterfall element & circular drive. The home's facade showcases board & batten siding, stone & striking black windows, gutters & trim. A covered front entry with a custom-built on-site front door & oversized 10-ft garage doors complete the curb appeal. Inside, every detail has been carefully designed & executed. Custom paneled walls conceal hidden features, including a discreet foyer closet & a hidden half bath accessed through the paneling along w/built-in storage for convenience. The open-concept living space is breathtaking, highlighted by soaring ceilings, exposed beams & a stunning central fireplace that anchors the home. The chef's kitchen is both beautiful & functional, featuring high-end cabinetry, a farmhouse sink, a large center island w/waterfall quartz edges & additional storage below. 1 wing of the home includes 2 guest bedrooms, a full bath & a cleverly enclosed laundry area finished walnut, keeping it completely out of sight. The primary suite offers a luxurious bath w/a walk-in shower, double vanities, walk-in closet, & a unique double-seater, lay-down soaking tub.

145 Monarca Dr, Middletown

500 Washington St Unit #4, Middletown
$89,900
2 Beds ⋅ 1 Baths ⋅ 24201126 MLS
*** Remodeled Home in Middletown Mobile Home Park *** Welcome to 500 Washington Street #4, a beautifully refurbished 1986 Peerless Supra offering fresh, move-in-ready living in a convenient Middletown location. This 14' x 60' home features 840 sq. ft., 2 bedrooms and 1 full bath, with extensive updates throughout. The brand-new kitchen shines with quartz countertops, new cabinetry, refrigerator, electric range, sink and faucet. Enjoy new flooring throughout, fresh interior paint, new closet doors and a new front door. The remodeled bath features a new tub/shower insert, vanity and toilet. Additional improvements include a brand-new central A/C system, new electrical line, added insulation, new skirting and stairs, plus new washer/dryer hookups. Thoughtfully refreshed from top to bottom, this inviting home combines modern finishes, comfort and low-maintenance living. Move right in and enjoy - Schedule your private showing today! (On new pad site - taxes to be determined. Purchaser to verify with local municipality.MMHP LLC - one of the parties to the LLC has an active real estate license.)

500 Washington St Unit #4, Middletown

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