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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
55 John Clarke Road Unit 23, Middletown
$415,000
1 Baths ⋅ 1422238 MLS ⋅ Newport Car Vaults BLDG.
Welcome to Newport Car Vaults! A unique opportunity designed for the automotive enthusiast looking for an exceptional space to showcase and enjoy their collection. This impressive condominium features striking red epoxy floors, climate-controlled heat and A/C, and a finished mezzanine overlooking the garage below an ideal space for relaxing and entertaining guests. Large windows provide abundant natural light along with beautiful water views, creating a bright and inviting atmosphere throughout the upper level. The unit also features a stylish full bathroom with a fully tiled black shower accented by elegant brass fixtures, perfectly complementing the contemporary design and bold red flooring. Whether you're looking to store, display, and enjoy your luxury, exotic, or classic cars, this distinctive Newport Car Vault offers an exceptional combination of style, comfort, and functionality. Please note: This condominium is not approved for residential or commercial use.

55 John Clarke Road Unit 23, 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
277 Carriage Crossing Ln Unit 277, Middletown
$220,000
1 Beds ⋅ 1 Baths ⋅ 24202361 MLS ⋅ Carriage Crossing BLDG.
Welcome to 277 Carriage Crossing Lane, where soaring ceilings, a charming loft, and a beautiful fireplace create a home you'll love coming back to. The inviting layout offers a comfortable, open feel with a cozy kitchen and versatile loft space perfect for a home office, reading nook, creative space, or relaxing retreat. Curl up by the fireplace on a cool evening or step outside and enjoy the community pool and hot tub when it's time to unwind. Warm, welcoming, and full of character, this is a home that truly feels like your own. Come see it and imagine yourself here!

277 Carriage Crossing Ln Unit 277, 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
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
130 Spencer Dr, Middletown
$349,000
5 Beds ⋅ 2 Baths ⋅ 24201926 MLS
Perfect 3-Bedroom Home Layout with 2 Bonus Flex Rooms/Offices! Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown
46 Middlefield St, Middletown
$369,900
3 Beds ⋅ 2 Baths ⋅ 24200173 MLS
Welcome to 46 Middlefield Street in Middletown! This beautifully remodeled home offers three bedrooms, two full bathrooms, and stylish updates throughout. The brand-new kitchen features sleek quartz countertops and modern finishes, creating an inviting space for cooking and entertaining. The refreshed interior combines contemporary style with comfortable, functional living spaces, making this home truly move-in ready. Conveniently located near shopping, dining, schools, and major routes, this property is an excellent opportunity for today's buyer. Schedule your private showing and see all this updated home has to offer!

46 Middlefield St, Middletown
53 Spring St, Middletown
$364,900
5 Beds ⋅ 3 Baths ⋅ 24199686 MLS
This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a generous sized 1 bed/1 bath unit. The units themselves are mostly updated, some with fresh paint and tile work tastefully done. A two car garage and off street parking provide ultimate convenience for owners and/or tenants. Lively flower beds decorate the front walkway, adding to the curb appeal. A back staircase seconds as small deck platforms overlooking the backyard. Whether living in one unit and renting the others for residual income, or adding this wonderful opportunity to your investment portfolio, this one is NOT to miss. Schedule your private showing today!

53 Spring St, Middletown
147 Ridge Rd, Middletown
$449,900
3 Beds ⋅ 2 Baths ⋅ 24199578 MLS
Welcome to 147 Ridge Rd, a stunning, completely remodeled home located in the highly desirable South Farms district of Middletown! This beautifully updated property has been renovated from top to bottom and is truly move-in ready. The heart of the home is the spectacular open-concept kitchen, featuring beautiful quartz countertops and seamless flow into a bright, light-filled living room with a decorative stone fireplace. Throughout the home, you'll find beautifully refinished hardwood floors and two beautifully updated bathrooms, each featuring elegant inlaid tile showers. The dining room features a slider to an impressive 16-foot deck, creating the perfect setting for indoor and outdoor entertaining, relaxing, and enjoying the private surroundings. Major updates include a new roof and windows, a newer furnace, and new electrical wiring and electrical panel. Every detail has been thoughtfully updated to create a comfortable, stylish, and modern home. This is a must-see property! Schedule your private showing today and experience everything 147 Ridge Rd has to offer.

147 Ridge Rd, Middletown
606 Congdon St W Unit 6, Middletown
$279,900
2 Beds ⋅ 2 Baths ⋅ 24199007 MLS ⋅ Luther Ridge At Middletown Condos BLDG.
Designed for convenient one-floor living, this well-maintained home features 2 bedrooms and 2 full bathrooms with a bright, open floor plan. The kitchen offers warm cherry cabinetry, a dishwasher, and plenty of functionality, while tile flooring throughout provides easy maintenance. Enjoy the comfort and efficiency of central air, natural gas heat, and natural gas hot water. This is a wonderful opportunity for those seeking a smaller community and low-maintenance lifestyle. One owner must be 60 years of age or older. Move right in and enjoy easy, single-level living!

606 Congdon St W Unit 6, Middletown
76 George St, Middletown
$429,000
3 Beds ⋅ 2 Baths ⋅ 24196637 MLS
Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on Boston Rd and the potential for an additional structure, subject to zoning and approvals. With generous land, flexible space, and multiple possibilities for future use, this property offers an excellent opportunity for homeowners, investors, or those looking to create additional living space. A lease-to-own option is also available. Don't miss this unique opportunity-bring your vision and explore the possibilities!

76 George St, Middletown
104 Bell St, Middletown
$415,000
4 Beds ⋅ 2 Baths ⋅ 24197069 MLS
Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical service, new AC unit and furnace, new oil tank, an updated well system, and a resurfaced bridge. The wooded, incredibly private lot offers endless potential - whether you envision expanded outdoor living, gardens, or simply the peace and quiet of your own retreat tucked away from the world. Despite the secluded feel, the property is easy to show and conveniently located with quick access to I-91, Wesleyan University, and downtown Middletown. With so much already done, this is a move-in ready home with room to dream on 2.6 acres. Buyer to verify flood zone designation and obtain flood insurance quotes prior to purchase. Agent/Owner.

104 Bell St, Middletown
23 Bayview Park Avenue, Middletown
$181,500
2 Beds ⋅ 1 Baths ⋅ 1419547 MLS
The first unit in Bayview Park to come on the market this year! Great condo alternative and the benefits of coastal living without the immense cost! This light-filled home includes 2 bedrooms and an open floor plan, central air, and loads of storage space. The location of the Bayview neighborhood makes everything Newport offers close! There are the beaches, downtown Newport, and easy on/off access to the Newport Bridge. Shopping is close and the bike path is just outside! The HOA fee includes water, sewer, and trash. Easy to show make your appointment today!

23 Bayview Park Avenue, Middletown
104 Higby Rd, Middletown
$399,999
3 Beds ⋅ 1 Baths ⋅ 24195038 MLS
Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown
18 Portland St, Middletown
$75,000
5 Beds ⋅ 3 Baths ⋅ 24182301 MLS
Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

18 Portland St, Middletown
714 Long Hill Rd Unit 714, Middletown
$225,000
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
36 Rising Trail Dr Unit 36, Middletown
$217,500
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

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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