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Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.

4 Beds ⋅ 4 Baths ⋅ 24183475 MLS

Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.

76 Thimble Rock Rd, Middletown

$849,900

Tucked away on a quiet, highly desirable cul-de-sac of only 7 homes in the sought-after South Farms district, this beautifully crafted 5-bedroom, 3.5-bathroom colonial features a stunning brick-front facade and exceptional curb appeal. Boasting a coveted 3-car attached garage, the home greets you with an abundance of natural light and gleaming hardwood floors flowing seamlessly throughout the main and upper living areas. The spacious, well-designed layout is perfect for both effortless entertaining and comfortable daily living, offering a generous floor plan with an ideal flow. The Ultimate Flexible Space: The true crown jewel of this property is the fully finished walk-out basement that adds an additional 1,070 sq/ft! Configured as a complete, self-contained in-law apartment, this private lower level includes its own separate entrance, full kitchen, living space, bedroom and bath-absolutely perfect for multi-generational living or long-term guests. Situated in a fantastic location, this home offers the generous space you need, the classic aesthetic you desire, and the unique floor plan flexibility that is so incredibly hard to find. Don't miss this versatile gem!

5 Beds ⋅ 4 Baths ⋅ 24177933 MLS

Tucked away on a quiet, highly desirable cul-de-sac of only 7 homes in the sought-after South Farms district, this beautifully crafted 5-bedroom, 3.5-bathroom colonial features a stunning brick-front facade and exceptional curb appeal. Boasting a coveted 3-car attached garage, the home greets you with an abundance of natural light and gleaming hardwood floors flowing seamlessly throughout the main and upper living areas. The spacious, well-designed layout is perfect for both effortless entertaining and comfortable daily living, offering a generous floor plan with an ideal flow. The Ultimate Flexible Space: The true crown jewel of this property is the fully finished walk-out basement that adds an additional 1,070 sq/ft! Configured as a complete, self-contained in-law apartment, this private lower level includes its own separate entrance, full kitchen, living space, bedroom and bath-absolutely perfect for multi-generational living or long-term guests. Situated in a fantastic location, this home offers the generous space you need, the classic aesthetic you desire, and the unique floor plan flexibility that is so incredibly hard to find. Don't miss this versatile gem!

29 Copper Beech Dr, Middletown

$225,000

Nestled in the highly sought-after Wesleyan Hills community, this well-maintained and affordable 3-bedroom condo offers the perfect blend of comfort, convenience, and privacy. Featuring an open floor plan, the home boasts an updated kitchen that flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. A sliding glass door leads to your own private deck overlooking a peaceful, quiet setting. The finished walk-out lower level provides additional flexible living space ideal for a family room, home office, or gym. Conveniently located just minutes from downtown Middletown, Wesleyan University, Middlesex Hospital, shopping, restaurants, and major highways, this property offers easy access to everything while still enjoying a serene neighborhood atmosphere. Enjoy nearby parks, hiking trails, golf courses, and the Connecticut River waterfront. A wonderful opportunity to own in one of Middletown's most desirable communities

3 Beds ⋅ 2 Baths ⋅ 24176493 MLS ⋅ Ridgely Condo BLDG.

Nestled in the highly sought-after Wesleyan Hills community, this well-maintained and affordable 3-bedroom condo offers the perfect blend of comfort, convenience, and privacy. Featuring an open floor plan, the home boasts an updated kitchen that flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. A sliding glass door leads to your own private deck overlooking a peaceful, quiet setting. The finished walk-out lower level provides additional flexible living space ideal for a family room, home office, or gym. Conveniently located just minutes from downtown Middletown, Wesleyan University, Middlesex Hospital, shopping, restaurants, and major highways, this property offers easy access to everything while still enjoying a serene neighborhood atmosphere. Enjoy nearby parks, hiking trails, golf courses, and the Connecticut River waterfront. A wonderful opportunity to own in one of Middletown's most desirable communities

714 Long Hill Rd Unit 714, Middletown

$679,900

Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

24175820 MLS

Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

27 Pleasant St, Middletown

$2,249,500

Investors dream - fully leased with value add potential! 18-unit corner brick building located on Main Street in the heart of Downtown Middletown, steps from gourmet restaurants and boutiques. Originally built in 1850, this 11,232 SQ FT building consists of 17 residential units and one ground level retail space. The retail space is leased to a mobile carrier/retailer through 2028 with annual rent escalation, allowing the new owner to focus on executing on the business plan for the 17 residential units. The building features four rare 2 beds, 2 bath units, seven 1-bedroom units, and six studio apartments. The building is currently fully leased, giving the new Owner an opportunity to capture the incredible rent upside over time while collecting rent income. The building has all separate gas boilers, huge unfinished basement and shared electricity. The units feature great layouts with nice natural light, high ceilings and large bedrooms with good closet space. The current owner has recently replaced some of the units windows, appliances and carpeting. Easy access to route 9 and a short drive/walk to Wesleyan University. This corner brick building is located near the beautiful, historic town center with over 7 walkable blocks of different restaurants and shops, featuring dozens of choices of dining, art, music, entertainment and unique finds. Neighborhood attractions include: Perkatory Coffee Roasters; Eli Cannons Tap Room; The Whey Station; Luce. Become part of this exciting tow

21 Baths ⋅ 24165225 MLS

Investors dream - fully leased with value add potential! 18-unit corner brick building located on Main Street in the heart of Downtown Middletown, steps from gourmet restaurants and boutiques. Originally built in 1850, this 11,232 SQ FT building consists of 17 residential units and one ground level retail space. The retail space is leased to a mobile carrier/retailer through 2028 with annual rent escalation, allowing the new owner to focus on executing on the business plan for the 17 residential units. The building features four rare 2 beds, 2 bath units, seven 1-bedroom units, and six studio apartments. The building is currently fully leased, giving the new Owner an opportunity to capture the incredible rent upside over time while collecting rent income. The building has all separate gas boilers, huge unfinished basement and shared electricity. The units feature great layouts with nice natural light, high ceilings and large bedrooms with good closet space. The current owner has recently replaced some of the units windows, appliances and carpeting. Easy access to route 9 and a short drive/walk to Wesleyan University. This corner brick building is located near the beautiful, historic town center with over 7 walkable blocks of different restaurants and shops, featuring dozens of choices of dining, art, music, entertainment and unique finds. Neighborhood attractions include: Perkatory Coffee Roasters; Eli Cannons Tap Room; The Whey Station; Luce. Become part of this exciting tow

668 Main St, Middletown

$499,900

This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set apart for added privacy, while two additional generously sized bedrooms and a second full bath provide flexibility for guests or home office needs. A dedicated laundry area and convenient entryway from the attached one-car garage enhance everyday functionality. Nathan Hale Estates is a thoughtfully planned residential community in Middletown, Connecticut, offering a quiet neighborhood setting while remaining conveniently close to shopping, dining, schools, parks, and major commuter routes. The central location provides easy access to the shoreline, making this an ideal place for you and your family. The builder offers generous allowances, allowing buyers to thoughtfully curate finishes and selections. Builder requires a one-time construction-to-permanent loan, financed by Elm Tree Funding.

3 Beds ⋅ 2 Baths ⋅ 24159101 MLS

This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set apart for added privacy, while two additional generously sized bedrooms and a second full bath provide flexibility for guests or home office needs. A dedicated laundry area and convenient entryway from the attached one-car garage enhance everyday functionality. Nathan Hale Estates is a thoughtfully planned residential community in Middletown, Connecticut, offering a quiet neighborhood setting while remaining conveniently close to shopping, dining, schools, parks, and major commuter routes. The central location provides easy access to the shoreline, making this an ideal place for you and your family. The builder offers generous allowances, allowing buyers to thoughtfully curate finishes and selections. Builder requires a one-time construction-to-permanent loan, financed by Elm Tree Funding.

Lot 4 Nathan Hale, Middletown

$217,500

Prime location near the pool & clubhouse - just in time for Summer! Welcome to 36 Rising Trail Drive, a beautifully maintained condo nestled in the desirable Westlake area of Middletown. This spacious unit offers a bright and open layout with generous living and dining areas, perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, ample counter space, and appliances. Upstairs, you'll find comfortably sized bedrooms, with plenty of closet space. Additional highlights include in-unit laundry, a private patio for outdoor relaxation, and convenient Carport. Located in a quiet, well-managed complex with easy access to shopping, restaurants, and major highways-this home offers the perfect blend of comfort, style, and location. Don't miss the opportunity to make it yours!

3 Beds ⋅ 2 Baths ⋅ 24111633 MLS

Prime location near the pool & clubhouse - just in time for Summer! Welcome to 36 Rising Trail Drive, a beautifully maintained condo nestled in the desirable Westlake area of Middletown. This spacious unit offers a bright and open layout with generous living and dining areas, perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, ample counter space, and appliances. Upstairs, you'll find comfortably sized bedrooms, with plenty of closet space. Additional highlights include in-unit laundry, a private patio for outdoor relaxation, and convenient Carport. Located in a quiet, well-managed complex with easy access to shopping, restaurants, and major highways-this home offers the perfect blend of comfort, style, and location. Don't miss the opportunity to make it yours!

36 Rising Trail Dr Unit 36, Middletown

$549,000

Award-winning builder, Reinhard Von Hollander proudly presents "The Cameron", one of his most sought-after models; sure to please the most discerning buyer. Quality and design meet as the home features a customizable, open floor plan, presenting future homeowners with an opportunity to make the space truly their own. It comes with 3 bedrooms and 2 full baths, including a spacious primary suite. This suite features a generous walk-in closet and a private bath with a double-sink setup. At the heart of the home, you'll find a sleek, modern kitchen graced with granite countertops, selected by the builder yet tailored to the buyer's preference. This is complemented by a seamless flow into the living areas, encouraging interaction and fostering a sense of community with guests and loved ones. The Cameron offers an exquisite blend of comfort and convenience. Modern charm throughout the home will give you a clean, welcoming feel. The oversized two-car garage not only has space for your vehicles but storage as well! Situated on just over an acre, there are plenty of opportunities to make this a one-of-a-kind oasis. Take advantage of this convenient location with Lyman Orchards and Lyman Orchard's Golf Club, parks, restaurants, shops, and major roadways and highways all within close proximity.

3 Beds ⋅ 2 Baths ⋅ 24014755 MLS

Award-winning builder, Reinhard Von Hollander proudly presents "The Cameron", one of his most sought-after models; sure to please the most discerning buyer. Quality and design meet as the home features a customizable, open floor plan, presenting future homeowners with an opportunity to make the space truly their own. It comes with 3 bedrooms and 2 full baths, including a spacious primary suite. This suite features a generous walk-in closet and a private bath with a double-sink setup. At the heart of the home, you'll find a sleek, modern kitchen graced with granite countertops, selected by the builder yet tailored to the buyer's preference. This is complemented by a seamless flow into the living areas, encouraging interaction and fostering a sense of community with guests and loved ones. The Cameron offers an exquisite blend of comfort and convenience. Modern charm throughout the home will give you a clean, welcoming feel. The oversized two-car garage not only has space for your vehicles but storage as well! Situated on just over an acre, there are plenty of opportunities to make this a one-of-a-kind oasis. Take advantage of this convenient location with Lyman Orchards and Lyman Orchard's Golf Club, parks, restaurants, shops, and major roadways and highways all within close proximity.

18-A Talcott Ridge Dr, Middletown

$369,900

Welcome to 58 Durant Terrace - a well-maintained 2-family home nestled in a quiet, desirable neighborhood just minutes from downtown Middletown, Wesleyan University, shopping, and dining. This versatile property offers two spacious units, each with 2 bedrooms, 1 full bath, bright living spaces, and hardwood flooring throughout. Ideal for investors or owner-occupants, live in one unit and rent the other to offset your mortgage! Features include: Separate entrances and utilities for each unit, updated kitchens and baths, generous backyard space perfect for entertaining or gardening. Off-street parking and potential garage or basement storage. Close to public transportation, parks, schools, and major highways. Whether you're looking to expand your rental portfolio or settle into a property with built-in income, 58 Durant Terrace is a rare find with solid potential - don't miss your chance to own this duplex gem in the heart of Middletown!

4 Beds ⋅ 2 Baths ⋅ 24124801 MLS

Welcome to 58 Durant Terrace - a well-maintained 2-family home nestled in a quiet, desirable neighborhood just minutes from downtown Middletown, Wesleyan University, shopping, and dining. This versatile property offers two spacious units, each with 2 bedrooms, 1 full bath, bright living spaces, and hardwood flooring throughout. Ideal for investors or owner-occupants, live in one unit and rent the other to offset your mortgage! Features include: Separate entrances and utilities for each unit, updated kitchens and baths, generous backyard space perfect for entertaining or gardening. Off-street parking and potential garage or basement storage. Close to public transportation, parks, schools, and major highways. Whether you're looking to expand your rental portfolio or settle into a property with built-in income, 58 Durant Terrace is a rare find with solid potential - don't miss your chance to own this duplex gem in the heart of Middletown!

58 Durant Ter, Middletown

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